Dimethylformamide → HCID 58615359, compound

HRID 853015Notes

Reaction equation

HRID 853015 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[S:12][CH2:13][CH3:14].C([Li])CCC.CN(C)[CH:22]=[O:23]>C1COCC1.[Cl-].[NH4+].C(OCC)(=O)C>[CH2:13]([S:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:22]=[O:23])[CH:3]=2)[N:8]=[CH:7][CH:6]=1)[CH3:14]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 58615381HCID 58615381, compoundHCID 178418339Butyllithium

Product 1

HCID 58615359HCID 58615359, compoundYield 51.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 6-bromo-4-ethylsulfanyl-quinoline (1.48 g, 5.5 mmol) in THF (60 mL) was added dropwise a 2.5M solution of n-butyllithium in hexanes (2.42 mL, 6.07 mmol, 1.1 equiv.) at −70° C. During the addition, the color of the solution was turned into a dark brown and this solution was stirred for 1 h at this temperature. Then, a solution of dimethylformamide (0.848 mL, 11 mmol) in THF (5 mL) was added dropwise. After addition, the mixture was allowed to warm to room temperature and stirred for 2 h. Then, the mixture was diluted with saturated ammonium chloride solution and the two layers were separated. The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the yellow solid which was dissolved in ethyl acetate (−10 mL) at hot condition and diluted with hexanes (−20 mL). After cooling in the refrigerator overnight, the solids were collected by filtration and washed with 10% ethyl acetate in hexanes. After drying in air, 0.614 g (51% yield) of 4-ethylsulfanyl-quinoline-6-carbaldehyde was isolated as a yellow solid: EI-HRMS m/e calcd for C12H11NOS (M+) 217.0561, found 217.0554.

Workup

  1. additionDuring the addition
  2. additionAfter addition
  3. stirringstirred for 2 h
  4. customthe two layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  6. washThe combined organic extracts were washed with brine solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationFiltration of the drying agent and removal of the solvent under the vacuum
  9. customgave the yellow solid which
  10. temperatureAfter cooling in the refrigerator overnight
  11. filtrationthe solids were collected by filtration
  12. washwashed with 10% ethyl acetate in hexanes
  13. customAfter drying in air

Sources & evidence

ORD record
ord-b7c9f7d750e94f10a653ebd3db6d6fbf
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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